EX-4.1



 Exhibit 4.1 

AMENDMENT NO. 1 TO SECOND AMENDED AND RESTATED 

LIMITED LIABILITY COMPANY AGREEMENT 

OF 
 TEEKAY OFFSHORE GP
L.L.C. 
 This AMENDMENT NO. 1 TO SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (this “Amendment”),
dated as of July 2, 2018, of Teekay Offshore GP L.L.C., a Marshall Islands non-resident domestic limited liability company (the “Company”), is by and among Teekay Holdings Limited, a Bermuda corporation (“TK”),
and Brookfield TK TOGP L.P., a Bermuda limited partnership (“Brookfield”). 
 WHEREAS, TK and Brookfield entered into that
Second Amended and Restated Limited Liability Company Agreement of the Company, dated as of September 25, 2017 (the “LLC Agreement”); 

WHEREAS, pursuant to Section 5.5 of the LLC Agreement, Brookfield has delivered a notice to TK of its intent to exercise its
option to purchase from TK two percent (2%) of the currently outstanding Shares (the “Option Shares”) in consideration of one million (1,000,000) Warrants (the “Purchased Warrants”); 

WHEREAS, concurrently with the execution of this Amendment, Brookfield will assign to TK (or TK’s designee) the Purchased Warrants; 

WHEREAS, the Company maintains a schedule of all Members setting forth the percentage of Shares held by each of them; and 

WHEREAS, TK and Brookfield now desire to amend the LLC Agreement as set forth in this Amendment to effect the sale and transfer from TK to
Brookfield of the Option Shares. 
 NOW, THEREFORE, for good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties hereby agree as follows: 
 1. Definitions. Capitalized terms used but not defined herein shall have the
meanings ascribed to them in the LLC Agreement. 
 2. Representations and Warranties of TK. TK hereby represents and warrants to
Brookfield that: 
 (a). TK is a corporation duly organized, validly existing and in good standing under the Laws of Bermuda. 

(b). All consents, approvals, authorizations and orders necessary for the execution and delivery by TK of this Amendment and for the sale and
transfer of the Option Shares to Brookfield have been obtained; and TK has all necessary corporate power and authority to enter into this Amendment and to sell and transfer the Option Shares to Brookfield. 







 (c). The sale and transfer of the Option Shares by TK to Brookfield and the compliance by TK with
this Amendment will not (A) conflict with or result in a breach or violation of any of the terms or provisions of, or constitute a default under, any statute, indenture, mortgage, deed of trust, loan agreement, lease or other agreement or
instrument to which TK is a party or by which TK is bound or to which any of the property or assets of TK is subject; (B) result in any violation of the provisions of the certificate of incorporation or bylaws or other similar organizational
documents of TK; or (C) violate any statute or any order, rule or regulation of any court or governmental agency or body having jurisdiction over TK or any of its subsidiaries or any property or assets of TK, except in the case of (A) and
(C) as would not impair the sale and transfer of the Option Shares by TK to Brookfield and the compliance by TK with this Amendment; and no consent, approval, authorization, order, registration or qualification of or with any such court or
governmental body or agency is required for the sale and transfer of the Option Shares by TK to Brookfield and the compliance by TK with this Amendment. 

(d). TK has good and valid title to the Option Shares, free and clear of all liens, encumbrances, equities or claims; and, upon the sale and
transfer of such Option Shares and payment therefor by the assignment by Brookfield to TK (or TK’s designee) of the Purchased Warrants, good and valid title to such Option Shares, free and clear of all liens, encumbrances, equities or claims,
will pass to Brookfield. 
 3. Representations and Warranties of Brookfield. Brookfield hereby represents and warrants to TK that:

 (a). Brookfield is a limited partnership duly formed, validly existing and in good standing under the Laws of Bermuda. 

(b). All consents, approvals, authorizations and orders necessary for the execution and delivery by Brookfield of this Amendment and for the
sale and transfer of the Purchased Warrants to TK (or TK’s designee) have been obtained; and Brookfield has all necessary limited partnership power and authority to enter into this Amendment and to sell and transfer the Purchased Warrants to TK
(or TK’s designee). 
 (c). The sale and transfer of the Purchased Warrants by Brookfield to TK (or TK’s designee) and the
compliance by Brookfield with this Amendment will not (A) conflict with or result in a breach or violation of any of the terms or provisions of, or constitute a default under, any statute, indenture, mortgage, deed of trust, loan agreement,
lease or other agreement or instrument to which Brookfield is a party or by which Brookfield is bound or to which any of the property or assets of Brookfield is subject; (B) result in any violation of the provisions of the organizational or
governing documents of Brookfield; or (C) violate any statute or any order, rule or regulation of any court or governmental agency or body having jurisdiction over Brookfield or any of its subsidiaries or any property or assets of Brookfield,
except in the case of (A) and (C) as would not impair the sale and transfer of the Purchased Warrants by Brookfield to TK (or TK’s designee) and the compliance by Brookfield with this Amendment; and no consent, approval,
authorization, order, registration or qualification of or with any such court or governmental body or agency is required for the sale and transfer of the Purchased Warrants by Brookfield to TK (or TK’s designee) and the compliance by Brookfield
with this Amendment. 

  
 2 








 (d). Brookfield has good and valid title to the Purchased Warrants, free and clear of all liens,
encumbrances, equities or claims; and, upon the sale and transfer of such Purchased Warrants and payment therefor by the assignment by TK to Brookfield of the Option Shares, good and valid title to such Purchased Warrants, free and clear of all
liens, encumbrances, equities or claims, will pass to TK (or TK’s designee). 
 4. Sale and Transfer of Option Shares. TK does
hereby sell, transfer, assign and deliver to Brookfield, and Brookfield does hereby accept, all of TK’s right, title and interest in the Option Shares, in exchange for, and against receipt by TK (or TK’s designee) of, the Purchased
Warrants. 
 5. Amendment to LLC Agreement. Schedule A hereto sets forth the Members Schedule as of the execution of this Amendment.

 5. No Further Amendment. Except as expressly provided in this Amendment, the terms and conditions of the LLC Agreement are and
remain in full force and effect. 
 6. Counterparts; Email and Facsimile. This Amendment may be executed in multiple counterparts,
each of which shall be deemed to be an original and shall be binding upon the Member who executed the same, but all of such counterparts shall constitute the same agreement. 

7. Governing Law. The provisions set forth in Section 13.2 of the LLC Agreement are hereby incorporated mutatis
mutandis. 
 *   *   *   * 

  
 3 








 IN WITNESS WHEREOF, the undersigned have executed this Amendment No. 1 to Second
Amended and Restated Limited Liability Company Agreement of Teekay Offshore GP L.L.C. as of the date first written above. 
  

			
	TEEKAY HOLDINGS LIMITED
		
	By:	 	  /s/ Edith Robinson

		 	 Name:  Edith Robinson

		 	 Title:   President



 [Signature Page to Amendment No. 1 to Second A&R Limited Liability Company Agreement]








 
			
	BROOKFIELD TK TOGP L.P.
	
	 BY ITS GENERAL PARTNER,

BROOKFIELD CAPITAL PARTNERS
 (BERMUDA)
LTD.

		
	By:	 	  /s/ Gregory E A Morrison

		 	Name: Gregory E A Morrison
		 	Title: Director


 [Signature Page to Amendment No. 1 to Second A&R Limited Liability Company Agreement]








 Schedule A 

Teekay Offshore GP L.L.C. 

Members Schedule 
 (as of
July 2, 2018) 
  

				                              	
	 	  	% of Shares
	 Teekay Holdings Limited

4th Floor, Belvedere Building

69 Pitts Bay Road

Hamilton, HM 08, Bermuda

Attn. Corporate Secretary

Facsimile:     (441) 298-2530

Email:      Edie.Robinson@teekay.com

 
 With a copy to (which copy alone shall not
constitute notice):
  
 Perkins Coie LLP

1120 NW Couch St., Tenth Floor

Portland, OR 97209

Attention:     David S. Matheson

            Gina K. Eiben

Facsimile:     (503) 346-2008

Email:      DMatheson@perkinscoie.com

         GEiben@perkinscoie.com
	  	 	49	% 
		
	 Brookfield TK TOGP L.P.

c/o Brookfield Capital Partners (Bermuda) Ltd.

73 Front Street, 5th Floor

Hamilton HM 12, Bermuda

Attention: Manager - Corporate Services

Facsimile:     (441) 296-4475

Email:      Jane.Sheere@brookfield.com

 
 With a copy to (which copy alone shall not
constitute notice):
	  	 	51	% 
		
	 Brookfield TK TOGP L.P.

c/o Brookfield Capital Partners Ltd.

Brookfield Place, Suite 300

181 Bay Street

Toronto, Ontario, M5J 2T3

Attention:     Ryan Szainwald, Senior Vice President

Facsimile:     (416) 369-2301

Email:      Ryan.Szainwald@brookfield.com

 
 With a copy to (which copy alone shall not
constitute notice):
  
 Kirkland & Ellis
LLP
 601 Lexington Avenue

New York, NY 10022

Attention:     Joshua N. Korff, Esq.

         Elazar Guttman, Esq.

         Ross M. Leff, Esq.
	  			


  
 A-1 









				                              	
	 Facsimile:     (212) 446-4900

Email:      JKorff@kirkland.com

         Elazar.Guttman@kirkland.com

         Ross.Leff@kirkland.com

 
	  			
		  	  
	  
	  

	 Total
	  	 	100	% 
		  	  
	  
	  



  
 A-2